Perfume compositions and 3,6-dicyclopentyl-ò-valero-lactone

ABSTRACT

A perfume composition containing a 3,6-disubstituted δ-valerolactone having fresh, fruity and floral musk-like fragrance, and 3,6-dicyclopentyl-δ-valerolactone. Specifically, the perfume composition contains a 3,6-disubstituted δ-valerolactone represented by formula [1]:  
                 
 
wherein at least one of R 1  and R 2  represents cyclopentyl group, cyclopentenyl group, cyclohexyl group or cyclohexenyl group and, when only one of R 1  and R 2  represents cyclopentyl group, cyclopentenyl group, cyclohexyl group or cyclohexenyl group, the other of R 1  and R 2  represents an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aralkyl group having 6 to 10 carbon atoms or an alkylaryl group having 6 to 10 carbon atoms; and aforesaid 3,6-Dicyclopentyl-δ-valerolactone is represented by formula [2]:

TECHNICAL FIELD

The present invention relates to a perfume composition and3,6-dicyclopentyl-δ-valerolactone. More specifically, the presentinvention relates to a perfume composition containing a3,6-disubstituted δ-valerolactone having cyclopentyl group,cyclopentenyl group, cyclohexyl group or cyclohexenyl group at least atone of the 3-position and the 6-position and having fresh, fruity andfloral musk-like fragrance, and 3,6-dicyclopentyl-δ-valerolactone.

BACKGROUND ART

In general, a substance utilized for providing fragrance is called aperfume. The perfume is divided into natural perfumes and syntheticperfumes based on the raw material. The natural perfume is said toinclude 1,500 types or more of the perfumes, and 100 to 150 types amongthe natural perfumes are useful in the market. The synthetic perfumesare manufactured by using cheap and abundant natural substances andpetroleum-based chemical products as the raw materials. The syntheticperfume is said to include 6,000 types or more of the perfumes, and 500to 600 types among the synthetic perfumes are frequently used. Sincenatural perfumes are, in general, more expensive than syntheticperfumes, the effort to develop synthetic perfumes has been continued,and the number of the synthetic perfumes is increasing every year.

The preference of users and consumers to the perfume products describedabove is varied depending on the age, the sex and the like. The numberof product types and the object of the use are rapidly expanding inaccordance with this variety. Perfumes with delicate varieties in thebasic tone, the depth, the width and the feel of volume in the fragranceare required.

A component of a perfume is one of physiologically active substances. Itis known that, when the chemical structure of the component is modified,the fragrance felt by a person differs from the mother compounddelicately or, occasionally, to a great degree. Therefore, it isimportant for obtaining a new perfume that analogues and derivatives ofknown perfume compounds are synthesized and their fragrance isevaluated.

The present invention has an object of providing a perfume compositioncontaining a 3,6-disubstituted δ-valerolactone having cyclopentyl group,cyclopentenyl group, cyclohexyl group or cyclohexenyl group at least atone of the 3-position and the 6-position and having fresh, fruity andfloral musk-like fragrance, and 3,6-dicyclopentyl-δ-valerolactone.

DISCLOSURE OF THE INVENTION

As the result of intensive studies by the present inventors to achievethe above object, it was found that a 3,6-disubstituted δ-valerolactonehaving cyclopentyl group, cyclopentenyl group, cyclohexyl group orcyclohexenyl group at least at one of the 3-position and the 6-positionhas the fresh, fruity and floral musk-like fragrance. The presentinvention has been completed based on the knowledge.

The present invention provides:(1) A 3,6-disubstituted δ-valerolactone represented by following formula[1]:

wherein at least one of R¹ and R² represents cyclopentyl group,cyclopentenyl group, cyclohexyl group or cyclohexenyl group and, whenonly one of R¹ and R² represents cyclopentyl group, cyclopentenyl group,cyclohexyl group or cyclohexenyl group, the other of R¹ and R²represents an alkyl group having 1 to 10 carbon atoms, an alkenyl grouphaving 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbonatoms, an aryl group having 6 to 10 carbon atoms, an aralkyl grouphaving 6 to 10 carbon atoms or an alkylaryl group having 6 to 10 carbonatoms;(2) 3,6-Dicyclopentyl-δ-valerolactone expressed by following formula[2]:

(3) A perfume composition containing a 3,6-disubstituted δ-valerolactonerepresented by following formula [1]:

wherein at least one of R¹ and R² represents cyclopentyl group,cyclopentenyl group, cyclohexyl group or cyclohexenyl group and, whenonly one of R¹ and R² represents cyclopentyl group, cyclopentenyl group,cyclohexyl group or cyclohexenyl group, the other of R¹ and R²represents an alkyl group having 1 to 10 carbon atoms, an alkenyl grouphaving 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbonatoms, an aryl group having 6 to 10 carbon atoms, an aralkyl grouphaving 6 to 10 carbon atoms or an alkylaryl group having 6 to 10 carbonatoms;(4) The perfume composition described in (3), wherein at least one of R¹and R² represents cyclopentyl group and, when only one of R¹ and R²represents cyclopentyl group, the other of R¹ and R² represents an alkylgroup having 1 to 10 carbon atoms;(5) The perfume composition described in (3), wherein at least one of R¹and R² represents cyclopentyl group and, when only one of R¹ and R²represents cyclopentyl group, the other of R¹ and R² represents n-pentylgroup;(6) The perfume composition described in (3), wherein R¹ and R²represent cyclopentyl groups;(7) The perfume composition described in (3), which contains the3,6-disubstituted δ-valerolactone in the concentration from 0.1 to 99%by weight; and(8) A process for producing the 3,6-disubstituted δ-valerolactone, asdefined in (1), which includes oxidizing a 2,5-disubstitutedcyclopentanone represented by following formula [3]:

wherein at least one of R¹ and R² represents cyclopentyl group,cyclopentenyl group, cyclohexyl group or cyclohexenyl group and, whenonly one of R¹ and R² represents cyclopentyl group, cyclopentenyl group,cyclohexyl group or cyclohexenyl group, the other of R¹ and R²represents an alkyl group having 1 to 10 carbon atoms, an alkenyl grouphaving 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbonatoms, an aryl group having 6 to 10 carbon atoms, an aralkyl grouphaving 6 to 10 carbon atoms or an alkylaryl group having 6 to 10 carbonatoms.

THE MOST PREFERRED EMBODIMENT TO CARRY OUT THE INVENTION

As the first embodiment, the present invention provides a perfumecomposition containing a 3,6-disubstituted δ-valerolactone representedby following formula [1]:

In the above formula [1], at least one of R¹ and R² representscyclopentyl group, cyclopentenyl group, cyclohexyl group or cyclohexenylgroup and, when only one of R¹ and R² represents cyclopentyl group,cyclopentenyl group, cyclohexyl group or cyclohexenyl group, the otherof R¹ and R² represents an alkyl group having 1 to 10 carbon atoms, analkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aralkylgroup having 6 to 10 carbon atoms or an alkylaryl group having 6 to 10carbon atoms. When R¹ represents cyclopentyl group, it is preferablethat R² represents cyclopentyl group, cyclohexyl group or an alkyl grouphaving 4 to 6 carbon atoms, more preferably cyclopentyl group or analkyl group having 5 carbon atoms, still more preferably cyclopentylgroup or n-pentyl group and most preferably cyclopentyl group. When R²represents cyclopentyl group, it is preferable that R¹ representscyclopentyl group, cyclohexyl group or an alkyl group having 4 to 6carbon atoms, more preferably cyclopentyl group or an alkyl group having5 carbon atoms, still more preferably cyclopentyl group or n-pentylgroup and most preferably cyclopentyl group.

As the second embodiment, the present invention provides3,6-dicyclopentyl-δ-valerolactone expressed by following formula [2]:

In the present invention, the process for producing the3,6-disubstituted δ-valerolactone represented by the formula [1] is notparticularly limited. For example, the 3,6-disubstituted δ-valerolactonerepresented by the formula [1] can be obtained via oxidation reaction ofa 2,5-disubstituted cyclopentanone represented by formula [3]:

When the 2,5-disubstituted cyclopentanone represented by the formula [3]is, for example, a compound in which both R¹ and R² representcyclopentyl group, the oxidation of the 2,5-disubstituted cyclopentanonecan be conducted, for example, as described in Japanese PatentApplication Laid-Open No. 2001-261609 and the United States PatentApplication Laid-Open No. 20030012799 in accordance with the reactionroute shown in formula [4]:

Specifically, 2-cyclopentylidenecyclopentanone is obtained bydehydration of 2-(1-hydroxycyclopentyl)cyclopentanone which is obtainedby the aldol condensation of two molecules of cyclopentanone in thepresence of an acid catalyst or a base catalyst. The obtained2-cyclopentylidenecyclo-pentanone is reacted with cyclopentanone in thepresence of an alkali such as sodium methylate to obtain2,5-dicyclopentylidenecyclopentanone, which is further converted into2,5-dicyclopentylcyclopentanone by hydrogenation of the carbon-carbondouble bond in the presence of a palladium catalyst or the like. Theobtained 2,5-dicyclopentylcyclo-pentanone is subjected to theBaeyer-Villiger oxidation with an inorganic peroxide such as ammoniumperoxodisulfate and potassium peroxo-disulfate or an organic peroxidesuch as m-chloroperbenzoic acid and benzoyl peroxide, whereby3,6-dicyclopentyl-δ-valerolactone can be obtained.

It is preferable that the amount of the peroxide used for theBaeyer-Villiger oxidation of 2,5-dicyclopentylcyclopentanone is 0.8 to 2moles per 1 mole of 2,5-dicyclopentylcyclopentanone. Examples of thesolvent for the reaction include water, sulfuric acid, acetic acid,propionic acid, valeric acid and dichloromethane. It is preferable thatthe amount by weight of the solvent is 0.3 to 30 times and morepreferably 0.5 to 20 times as much as the amount by weight of2,5-dicyclopentylcyclo-pentanone. It is preferable that the reactiontemperature is 10 to 80° C. and more preferably 20 to 40° C. It ispreferable in the Baeyer-Villiger oxidation that the peroxide is addeddropwise while the solution of 2,5-dicyclopentylcyclopentanone isstirred to prevent rapid elevation of the reaction temperature.

When the 2,5-disubstituted cyclopentanone represented by the formula [3]is a compound in which one of R¹ and R² represents cyclopentyl group andthe other of R¹ and R² represents n-pentyl group, the reaction can beconducted, for example, as described in WO 03/011803, in accordance withthe reaction route shown in formula [5]:

Specifically, 2-pentylidenecyclopentanone is obtained by dehydration of2-(1-hydroxypentyl)cyclopentanone which is obtained by the aldolcondensation of cyclopentanone and valeraldehyde in the presence of anacid catalyst or a base catalyst. The obtained2-pentylidenecyclo-pentanone is converted into 2-n-pentylcyclopentanoneby hydrogenation of the carbon-carbon double bond in the presence of apalladium catalyst or the like. The obtained 2-n-pentylcyclopentanone isreacted with cyclopentanone in the presence of an alkali such as sodiummethylate to obtain 2-cyclopentylidene-5-n-pentylcyclopentanone, whichis further converted into 2-cyclopentyl-5-n-pentylcyclopentanone byhydrogenation of the carbon-carbon double bond in the presence of apalladium catalyst or the like. The obtained2-cyclopentyl-5-n-pentylcyclopentanone is subjected to theBaeyer-Villiger oxidation with an inorganic peroxide such as ammoniumperoxodisulfate and potassium peroxodisulfate or an organic peroxidesuch as m-chloroperbenzoic acid and benzoyl peroxide, whereby a mixtureof 3-cyclopentyl-6-n-pentyl-δ-valerolactone and3-n-pentyl-6-cyclopentyl-5-valerolactone can be obtained.

It is preferable that the amount of the peroxide used in theBaeyer-Villiger oxidation of 2-cyclopentyl-5-n-pentylcyclopentanone is0.8 to 2 moles per 1 mole of 2-cyclopentyl-5-n-pentylcyclopentanone.Examples of the solvent for the reaction include water, sulfuric acid,acetic acid, propionic acid, valeric acid and dichloromethane. It ispreferable that the amount by weight of the solvent is 0.3 to 30 timesand more preferably 0.5 to 20 times as much as the amount by weight of2-cyclopentyl-5-n-pentylcyclopentanone. It is preferable that thereaction temperature is 10 to 80° C. and more preferably 20 to 40° C. Itis preferable in the Baeyer-Villiger oxidation that the peroxide isadded dropwise while the solution of2-cyclopentyl-5-n-pentylcyclopentanone is stirred to prevent rapidelevation of the reaction temperature.

The perfume composition of the present invention contains the3,6-disubstituted δ-valerolactone represented by the formula [1]. The3,6-disubstituted δ-valerolactone represented by the formula [1] may beused singly or in combination of two or more types. The composition ofthe present invention may further contain other perfume components,other solvents and the like, where necessary. It is preferable that thecontent of the 3,6-disubstituted δ-valerolactone represented by theformula [1] in the composition of the present invention is 0.1 to 99% byweight and more preferably 0.5 to 90% by weight.

The other perfume components to be contained in the composition of thepresent invention are not particularly limited. Examples of the otherperfume components include animal-based perfume components such as musk(muscone), civet (civetone), castrium (tetrahydroionone, castrin,acetophenone), ambergris (ambrein, amber oxide and γ-ionone); essentialoils such as ambrette seed oil, ylang-ylang oil, oak moss oil, opoponaxoil, orris oil, olibanum oil, orange oil, orange flower oil, galbanumoil, clary sage oil, clove oil, grape fruit oil, coriander oil, jasminoil, spearmint oil, cedarwood oil, geranium oil, thyme oil, tuberoseoil, tree moss oil, tonka bean oil, nutmeg oil, neroli oil, nerolibigarade oil, patchouli oil, vanilla oil, hyacinth oil, sandalwood oil,petitgrain oil, bay oil, vetivar oil, bergamot oil, peppermint oil, perubalsam oil, benzoin oil, pepper oil, mandaline oil, mimosa oil, limeoil, lavandin oil, labdanum oil, lavender oil, lemon oil and rose oil;and synthetic perfumes such as ethylene brassylate, eugenol, galaxolid,coumarin, geraniol, vetiveryl acetate, benzyl acetate, linalyl acetate,santalol, citral, citronellol, methyl dihydrojasmonate, aliphaticaldehydes, cis-jasmone, methyl jasmonate, damascone, damascenone,α-terpineol, vanillin, hydroxy-citronellal, phenylacetaldehyde,β-phenylethyl alcohol, α-hexyl-cinnamaldehyde, cis-3-hexenol,heliotropine, vertofix, musk-ketone, methylionone, 1-menthol, linalool,d-limonene, lily aldehyde and rose oxide. These other perfume componentsmay be used singly or in combination of two or more types. In thecomposition of the present invention, it is preferable that the amountof the other perfume component is 0.1 to 500 parts by weight and morepreferably 1 to 200 parts by weight per 1 part by weight of the3,6-disubstituted δ-valerolactone represented by the formula [1].

The perfume composition of the present invention may be mixed with asolvent component. By mixing with the solvent component, the strength asthe perfume can be adjusted, and permeability of the composition into asupport can be enhanced when the support is impregnated with thecomposition. The solvent component is not particularly limited. Examplesof the solvent components include ethanol, polyhydric alcohols,paraffin, glycol ethers and esters of phthalic acid. When the support isimpregnated with the composition using water as the medium, it ispreferable that a surfactant is mixed. The composition of the presentinvention may contain a fixative as the perfume component to adjust thetime of maintaining the fragrance.

The perfume composition of the present invention can be used fordetergents, softeners for fiber products, products for softening fiberproducts, softener products for fibers on dryer use, creams, emulsions,cosmetic powders, talc, body lotions, products for hair dressing, soaps,shampoos, rinses, indoor fragrances, bathing agents, tooth paste aerosolproducts and the like.

EXAMPLES

The present invention will be described more specifically with referenceto examples in the following. However, the present invention is notlimited to the examples.

For the 3,6-disubstituted δ-valerolactone obtained in Examples, theinfrared absorption spectrum, nuclear magnetic resonance spectrum andmass spectrum were measured using a infrared spectrophotometer[manufactured by NIPPON BUNKO KOGYO Co., Ltd; REPORT-100], a nuclearmagnetic resonance apparatus [manufactured by VARIAN JAPAN Co., Ltd;GEMINI 2000] and a mass analyzer [manufactured by NIPPON DENSHI Co.,Ltd.; JMS-7000], respectively.

Example 1 Synthesis of 3,6-dicyclopentyl-δ-valerolactone

Into a 500 ml four-necked flask equipped with a stirrer and a refluxcondenser, 33 ml of water and 98 ml of a concentrated sulfuric acid wereplaced under cooling with ice. Then, 66.3 g (0.245 moles) of potassiumperoxodisulfate and 110 ml of water were added successively. To theresultant mixture, 33.0 g (0.15 moles) of2,5-dicyclopentylcyclopentanone obtained in accordance with the processdescribed in Japanese Patent Application Laid-Open No. 2001-261609 wasadded dropwise over 40 minutes at room temperature, and the obtainedmixture was stirred for 40 hours. The reaction mixture was treated byextraction twice each with 150 ml of diethyl ether. The diethyl etherlayer was combined, washed successively with a saturated aqueoussolution of sodium hydrogencarbonate and a saturated aqueous solution ofsodium chloride, and dried with anhydrous magnesium sulfate. Theresultant mixture was filtered, and the filtrate was concentrated. Theresultant concentrate was treated in accordance with the silica gelcolumn chromatography (the elution solvent: ethyl acetate:n-hexane=1:10by volume). After recrystallization from a 75% by weight aqueoussolution of ethanol, 13.4 g (56.8 mmoles) of3,6-dicyclopentyl-δ-valerolactone having a purity of 99% was obtained aswhite leaf-shaped crystals. The yield was 38%.

The obtained 3,6-dicyclopentyl-δ-valerolactone had fresh, fruity andfloral musk-like fragrance.

¹H-NMR (500 MHz, CDCl₃, TMS, δ ppm): 1.06-1.33 (m, 4H), 1.33-2.35 (m,18H), 2.35-2.50 (m, 1H), 3.95-4.13 (m, 1H)

IR (KBr, cm⁻¹): 1720 (C═O)

MS (EI, 70 mV): 236, 193, 167, 150, 121, 108, 96, 81, 67, 54, 41

Example 2 Synthesis of 3,6-dicyclopentyl-δ-valerolactone

Into a 100 ml four-necked flask equipped with a stirrer and a refluxcondenser, 50 ml of dichloromethane and 4.4 g (20 mmoles) of2,5-dicyclopentylcyclopentanone were placed. While the resultantsolution was kept at the room temperature, 7.3 g (33.8 mmoles) of a 80%by weight m-chloroperbenzoic acid was added, and the obtained mixturewas stirred at the room temperature for 48 hours. The formedprecipitates were removed by filtration, and the organic layer waswashed successively with a saturated aqueous solution of sodiumhydrogencarbonate and a saturated aqueous solution of sodium chloride,and then dried with anhydrous magnesium sulfate. The resultant mixturewas filtered, and the filtrate was concentrated. The resultantconcentrate was treated in accordance with the silica gel columnchromatography (the elution solvent: ethyl acetate:n-hexane=1:10 byvolume). After recrystallization from a 75% by weight aqueous solutionof ethanol, 2.4 g (10.2 mmoles) of 3,6-dicyclopentyl-δ-valerolactonehaving a purity of 99% was obtained as white leaf-shaped crystals. Theyield was 51%.

Example 3 Synthesis of 3-cyclopentyl-6-n-pentyl-δ-valerolactone and3-n-pentyl-6-cyclopentyl-δ-valerolactone

The reaction was conducted in accordance with the same procedures asthose conducted in Example 1 except that 33.0 g (0.149 moles) of2-cyclopentyl-5-n-pentylcyclopentanone obtained in accordance with theprocess described in WO 03/011803 was used in place of 33.0 g of2,5-dicyclopentylcyclopentanone. A mixture of3-cyclopentyl-6-n-pentyl-δ-valerolactone and3-n-pentyl-6-cyclopentyl-δ-valerolactone, having a purity of 99%, in anamount of 10.2 g (42.9 mmoles) was obtained as white leaf-shapedcrystals. The yield was 28%.

The obtained mixture of 3-cyclopentyl-6-n-pentyl-δ-valerolactone and3-n-pentyl-6-cyclopentyl-δ-valerolactone had fresh, sweet and floralmusk-like fragrance.

¹H-NMR (500 MHz, CDCl₃, TMS, δ ppm): 0.85 (t, 3H), 1.16-1.44 (m, 8H),1.44-1.74 (m, 8H), 1.80-2.16 (m, 5H), 2.28-2.48 (m, 1H), 4.00-4.26 (m,1H)

IR (KBr, cm⁻¹): 1722, 1725 (C═O)

MS (EI, 70 mV): 238, 195, 169, 150, 123, 108, 96, 81, 67, 54, 41

Example 4 Synthesis of 3-cyclopentyl-6-n-pentyl-δ-valerolactone and3-n-pentyl-6-cyclopentyl-δ-valerolactone

The reaction was conducted in accordance with the same procedures asthose conducted in Example 2 except that 4.4 g (19.8 mmoles) of2-cyclopentyl-5-n-pentylcyclopentanone was used in place of 4.4 g of2,5-dicyclopentylcyclopentanone. A mixture of3-cyclopentyl-6-n-pentyl-δ-valerolactone and3-n-pentyl-6-cyclopentyl-δ-valerolactone having a purity of 99%, in anamount of 2.0 g (8.4 mmoles) was obtained as white leaf-shaped crystals.The yield was 42%.

Example 5 Preparation of a Sweet and Floral Perfume Composition of theSemioriental Type

A perfume composition was prepared in accordance with the formulation ofperfume components shown in Table 1 and evaluated by seven members ofthe evaluation panel.

Comparative Example 1

A perfume composition was prepared in accordance with the sameformulation as that shown in Table 1 except that ethylene brasilate wasused in place of 3,6-dicyclopentyl-δ-valerolactone and evaluated byseven members of the evaluation panel simultaneously with the evaluationof the perfume composition prepared in Example 1.

The formulation for the perfume composition prepared in Example 5 isshown in Table 1, and the results of the evaluation in Example 5 andComparative Example 1 are shown in Table 2. TABLE 1 Component of perfumeAmount (part by weight) ZEPPIN (NIPPON ZEON) 2 cis-3-Hexenyl acetate(NIPPON ZEON) 3 γ-Undecalactone 4 Ethyl linalool (GIVAUDAN) 4 Linalylacetate 10 Styralyl acetate 10 AQUANAL (QUEST) 10 Dihydromyrcenol 14Anisaldehyde 4 Benzyl acetate 6 Phenylhexanol 10 Cinnamic alcohol 10Dimethylbenzylcarbinyl acetate 10 Rhodinol 20 Florosa (QUEST) 30 Kovanol(TAKASAGO) 70 SUPER CEPIONATE (NIPPON ZEON) 90 Phenoxyethyl alcohol 165Eugenol 2 α-Ionone 10 EBANOL (GIVAUDAN) 143,6-Dicyclopentyl-δ-valerolactone 19 ISO - E - Super 180 Methylionone200 AMBROXAN (HENKEL) 4 Ethylvanillin 4 Heliotropine 15Cyclopentadecanolide 80 Total 1,000

TABLE 2 Member of evaluation Comparative panel Example 5 Example 1 Aelegant top note with weak as overall feel of volume impression Bpowdery with slight insufficient in sweetness sweetness C elegantlyfloral feeling, sour feeling, significantly significantly D excellent inquickness deficient in feel of volume E more excellent in Example strongchemical smell F harmony with combination no depth felt of fragrances Gelegant, atmosphere of stiffness felt a high grade

As shown by the results in Table 2, all members of the evaluation panelevaluated the perfume composition in Example 5 using3,6-dicyclopentyl-δ-valerolactone as more excellent than the perfumecomposition in Comparative Example 1 using ethylene brasilate which isproduced in a great amount as the macrocyclic musk.

INDUSTRIAL APPLICABILITY

The perfume composition of the present invention contains the3,6-disubstituted δ-valerolactone having cyclopentyl group,cyclopentenyl group, cyclohexyl group or cyclohexenyl group at least atone of the 3-position and the 6-position, emits fresh, sweet and floralmusk-like fragrance and is useful as the synthetic perfume. The3,6-dicyclopentyl-δ-valerolactone of the present invention is thecompound having fresh, sweet and floral musk-like fragrance.

1. A 3,6-disubstituted δ-valerolactone represented by following formula[1]:

wherein at least one of R¹ and R² represents cyclopentyl group,cyclopentenyl group, cyclohexyl group or cyclohexenyl group and, whenonly one of R¹ and R² represents cyclopentyl group, cyclopentenyl group,cyclohexyl group or cyclohexenyl group, the other of R¹ and R²represents an alkyl group having 1 to 10 carbon atoms, an alkenyl grouphaving 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbonatoms, an aryl group having 6 to 10 carbon atoms, an aralkyl grouphaving 6 to 10 carbon atoms or an alkylaryl group having 6 to 10 carbonatoms.
 2. 3,6-Dicyclopentyl-δ-valerolactone expressed by followingformula [2]:


3. A perfume composition comprising a 3,6-disubstituted δ-valerolactonerepresented by following formula [1]:

wherein at least one of R¹ and R² represents cyclopentyl group,cyclopentenyl group, cyclohexyl group or cyclohexenyl group and, whenonly one of R¹ and R² represents cyclopentyl group, cyclopentenyl group,cyclohexyl group or cyclohexenyl group, the other of R¹ and R²represents an alkyl group having 1 to 10 carbon atoms, an alkenyl grouphaving 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbonatoms, an aryl group having 6 to 10 carbon atoms, an aralkyl grouphaving 6 to 10 carbon atoms or an alkylaryl group having 6 to 10 carbonatoms.
 4. The perfume composition according to claim 3, wherein said atleast one of R¹ and R² represents cyclopentyl group and, when said onlyone of R¹ and R² represents cyclopentyl group, the other of R¹ and R²represents an alkyl group having 1 to 10 carbon atoms.
 5. The perfumecomposition according to claim 3, wherein said at least one of R¹ and R²represents cyclopentyl group and, when said only one of R¹ and R²represents cyclopentyl group, the other of R¹ and R² represents n-pentylgroup.
 6. The perfume composition according to claim 3, wherein said R¹and said R² represent cyclopentyl groups.
 7. The perfume compositionaccording to claim 3, which comprises the 3,6-disubstitutedδ-valerolactone in the concentration from 0.1 to 99% by weight.
 8. Aprocess for producing the 3,6-disubstituted δ-valerolactone, as definedin claim 1, which comprises oxidizing a 2,5-disubstituted cyclopentanonerepresented by following formula [3]:

wherein at least one of R¹ and R² represents cyclopentyl group,cyclopentenyl group, cyclohexyl group or cyclohexenyl group and, whenonly one of R¹ and R² represents cyclopentyl group, cyclopentenyl group,cyclohexyl group or cyclohexenyl group, the other of R¹ and R²represents an alkyl group having 1 to 10 carbon atoms, an alkenyl grouphaving 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbonatoms, an aryl group having 6 to 10 carbon atoms, an aralkyl grouphaving 6 to 10 carbon atoms or an alkylaryl group having 6 to 10 carbonatoms.